CN116194513A - Wire enamel composition comprising polyamideimide - Google Patents
Wire enamel composition comprising polyamideimide Download PDFInfo
- Publication number
- CN116194513A CN116194513A CN202180064490.XA CN202180064490A CN116194513A CN 116194513 A CN116194513 A CN 116194513A CN 202180064490 A CN202180064490 A CN 202180064490A CN 116194513 A CN116194513 A CN 116194513A
- Authority
- CN
- China
- Prior art keywords
- polyamideimide
- composition
- diisocyanate
- polyamideimide resin
- wire
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 239000004962 Polyamide-imide Substances 0.000 title claims abstract description 38
- 229920002312 polyamide-imide Polymers 0.000 title claims abstract description 38
- 239000000203 mixture Substances 0.000 title claims abstract description 35
- 210000003298 dental enamel Anatomy 0.000 title description 11
- 229920005989 resin Polymers 0.000 claims abstract description 24
- 239000011347 resin Substances 0.000 claims abstract description 24
- BNXZHVUCNYMNOS-UHFFFAOYSA-N 1-butylpyrrolidin-2-one Chemical compound CCCCN1CCCC1=O BNXZHVUCNYMNOS-UHFFFAOYSA-N 0.000 claims abstract description 12
- 238000000576 coating method Methods 0.000 claims description 11
- 239000002105 nanoparticle Substances 0.000 claims description 10
- 239000011248 coating agent Substances 0.000 claims description 9
- 150000008064 anhydrides Chemical class 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- 125000005442 diisocyanate group Chemical group 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 5
- 150000002763 monocarboxylic acids Chemical class 0.000 claims description 5
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 4
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 3
- 235000019253 formic acid Nutrition 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 239000003607 modifier Substances 0.000 claims description 3
- 235000011054 acetic acid Nutrition 0.000 claims description 2
- 235000019260 propionic acid Nutrition 0.000 claims description 2
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 2
- 150000003627 tricarboxylic acid derivatives Chemical class 0.000 claims 2
- 238000009413 insulation Methods 0.000 abstract 1
- 239000002904 solvent Substances 0.000 description 20
- 238000006243 chemical reaction Methods 0.000 description 18
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 13
- 229920000642 polymer Polymers 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 229910052782 aluminium Inorganic materials 0.000 description 6
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 6
- 239000007822 coupling agent Substances 0.000 description 6
- 229910044991 metal oxide Inorganic materials 0.000 description 5
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000004411 aluminium Substances 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- 150000004706 metal oxides Chemical class 0.000 description 4
- LCEDQNDDFOCWGG-UHFFFAOYSA-N morpholine-4-carbaldehyde Chemical compound O=CN1CCOCC1 LCEDQNDDFOCWGG-UHFFFAOYSA-N 0.000 description 4
- -1 naphthalene tricarboxylic anhydride Chemical class 0.000 description 4
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- KYWXRBNOYGGPIZ-UHFFFAOYSA-N 1-morpholin-4-ylethanone Chemical compound CC(=O)N1CCOCC1 KYWXRBNOYGGPIZ-UHFFFAOYSA-N 0.000 description 2
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 2
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 150000004984 aromatic diamines Chemical class 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 239000008199 coating composition Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 230000036461 convulsion Effects 0.000 description 2
- 239000006184 cosolvent Substances 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical compound C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 description 2
- 238000010292 electrical insulation Methods 0.000 description 2
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 2
- 125000005462 imide group Chemical group 0.000 description 2
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 239000005056 polyisocyanate Substances 0.000 description 2
- 229920001228 polyisocyanate Polymers 0.000 description 2
- 239000002952 polymeric resin Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 229910000077 silane Inorganic materials 0.000 description 2
- 239000010703 silicon Substances 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 229920003002 synthetic resin Polymers 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 239000010936 titanium Substances 0.000 description 2
- 229910052719 titanium Inorganic materials 0.000 description 2
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 2
- 150000003628 tricarboxylic acids Chemical class 0.000 description 2
- 229910052726 zirconium Inorganic materials 0.000 description 2
- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 description 1
- MTZUIIAIAKMWLI-UHFFFAOYSA-N 1,2-diisocyanatobenzene Chemical compound O=C=NC1=CC=CC=C1N=C=O MTZUIIAIAKMWLI-UHFFFAOYSA-N 0.000 description 1
- ZXHZWRZAWJVPIC-UHFFFAOYSA-N 1,2-diisocyanatonaphthalene Chemical compound C1=CC=CC2=C(N=C=O)C(N=C=O)=CC=C21 ZXHZWRZAWJVPIC-UHFFFAOYSA-N 0.000 description 1
- OVBFMUAFNIIQAL-UHFFFAOYSA-N 1,4-diisocyanatobutane Chemical compound O=C=NCCCCN=C=O OVBFMUAFNIIQAL-UHFFFAOYSA-N 0.000 description 1
- CDMDQYCEEKCBGR-UHFFFAOYSA-N 1,4-diisocyanatocyclohexane Chemical compound O=C=NC1CCC(N=C=O)CC1 CDMDQYCEEKCBGR-UHFFFAOYSA-N 0.000 description 1
- VZXPHDGHQXLXJC-UHFFFAOYSA-N 1,6-diisocyanato-5,6-dimethylheptane Chemical compound O=C=NC(C)(C)C(C)CCCCN=C=O VZXPHDGHQXLXJC-UHFFFAOYSA-N 0.000 description 1
- UTFSEWQOIIZLRH-UHFFFAOYSA-N 1,7-diisocyanatoheptane Chemical compound O=C=NCCCCCCCN=C=O UTFSEWQOIIZLRH-UHFFFAOYSA-N 0.000 description 1
- XEOANEVNYYOZOX-UHFFFAOYSA-N 1-isocyanato-4-(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=C(N=C=O)C=C1 XEOANEVNYYOZOX-UHFFFAOYSA-N 0.000 description 1
- LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical group NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 description 1
- JUMUEPDLAXMYHG-UHFFFAOYSA-N 3-[5-(4-aminophenyl)-1,3,4-thiadiazol-2-yl]aniline Chemical compound C1=CC(N)=CC=C1C1=NN=C(C=2C=C(N)C=CC=2)S1 JUMUEPDLAXMYHG-UHFFFAOYSA-N 0.000 description 1
- CSOGSFLQPUMFOB-UHFFFAOYSA-N 4-(4-aminocyclohexyl)aniline Chemical compound C1CC(N)CCC1C1=CC=C(N)C=C1 CSOGSFLQPUMFOB-UHFFFAOYSA-N 0.000 description 1
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 1
- ZEJGMGVVOLRJKV-UHFFFAOYSA-N 4-[5-(4-aminophenyl)-1,3,4-thiadiazol-2-yl]aniline Chemical compound C1=CC(N)=CC=C1C1=NN=C(C=2C=CC(N)=CC=2)S1 ZEJGMGVVOLRJKV-UHFFFAOYSA-N 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 1
- 239000005058 Isophorone diisocyanate Substances 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- 150000004729 acetoacetic acid derivatives Chemical class 0.000 description 1
- 229910052768 actinide Inorganic materials 0.000 description 1
- 150000001255 actinides Chemical class 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000004103 aminoalkyl group Chemical group 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 150000003972 cyclic carboxylic anhydrides Chemical class 0.000 description 1
- KSFBTBXTZDJOHO-UHFFFAOYSA-N diaminosilicon Chemical compound N[Si]N KSFBTBXTZDJOHO-UHFFFAOYSA-N 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- KORSJDCBLAPZEQ-UHFFFAOYSA-N dicyclohexylmethane-4,4'-diisocyanate Chemical compound C1CC(N=C=O)CCC1CC1CCC(N=C=O)CC1 KORSJDCBLAPZEQ-UHFFFAOYSA-N 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- LTYMSROWYAPPGB-UHFFFAOYSA-N diphenyl sulfide Chemical compound C=1C=CC=CC=1SC1=CC=CC=C1 LTYMSROWYAPPGB-UHFFFAOYSA-N 0.000 description 1
- 239000012777 electrically insulating material Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 229910052733 gallium Inorganic materials 0.000 description 1
- 229910052732 germanium Inorganic materials 0.000 description 1
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 description 1
- FAHBNUUHRFUEAI-UHFFFAOYSA-M hydroxidooxidoaluminium Chemical compound O[Al]=O FAHBNUUHRFUEAI-UHFFFAOYSA-M 0.000 description 1
- 239000011810 insulating material Substances 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 229910052747 lanthanoid Inorganic materials 0.000 description 1
- 150000002602 lanthanoids Chemical class 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000011342 resin composition Substances 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
- 150000004867 thiadiazoles Chemical group 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 125000005369 trialkoxysilyl group Chemical group 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/14—Polyamide-imides
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/1003—Preparatory processes
- C08G73/1007—Preparatory processes from tetracarboxylic acids or derivatives and diamines
- C08G73/1028—Preparatory processes from tetracarboxylic acids or derivatives and diamines characterised by the process itself, e.g. steps, continuous
- C08G73/1032—Preparatory processes from tetracarboxylic acids or derivatives and diamines characterised by the process itself, e.g. steps, continuous characterised by the solvent(s) used
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/1003—Preparatory processes
- C08G73/1035—Preparatory processes from tetracarboxylic acids or derivatives and diisocyanates
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
- C08K3/20—Oxides; Hydroxides
- C08K3/22—Oxides; Hydroxides of metals
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
- C08K5/3415—Five-membered rings
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D177/00—Coating compositions based on polyamides obtained by reactions forming a carboxylic amide link in the main chain; Coating compositions based on derivatives of such polymers
- C09D177/06—Polyamides derived from polyamines and polycarboxylic acids
- C09D177/08—Polyamides derived from polyamines and polycarboxylic acids from polyamines and polymerised unsaturated fatty acids
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
- H01B3/00—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties
- H01B3/18—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances
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Abstract
The present invention relates to a polyamideimide composition which is very suitable for use as primary insulation for wires. The composition comprises 55 to 65pbw of N-butyl pyrrolidone, 25 to 40pbw of a polyamideimide resin, 0 to 20pbw of other components, wherein the polyamideimide resin has a Mw between 10000 to 40000g/mol (daltons) and a Mw/Mn ratio between 1.1 to 2.
Description
The present invention relates to a wire enamel (wire end) composition comprising a polyamideimide.
In transformers, generators and motors, the electrically insulating material protecting the copper or aluminium wires is a thin coating of high performance polymer. The coating, known as primary electrical insulation or wire enamel, is as thin as possible to obtain the maximum number of turns in each slot space. Sufficient thermal, mechanical and electrical properties must be maintained. One such polymer used as primary electrical insulation is a poly (amide-imide) or polyamideimide resin. Prominent features include high thermal performance, chemical and abrasion resistance, and low coefficient of friction.
The polyamideimide coating compositions form flexible and durable films and are particularly useful as wire enamels, varnishes, adhesives for laminates, non-stick coatings, polyamideimides, and the like. These compositions are known in particular for their long-term high-temperature capability (=220 ℃ (430F)).
In GB570858, it is disclosed to prepare an aromatic polyamideimide resin by reacting trimellitic anhydride and an aromatic diamine. Typically these reactions are carried out in aprotic solvents such as N-methylpyrrolidone (NMP), dimethylacetamide (DMAc) or Dimethylformamide (DMF).
In US3541038, the preparation of aromatic polyamideimide resins using trimellitic anhydride and a polyisocyanate, preferably a diisocyanate, is described. This reaction is preferably carried out using N-methylpyrrolidone (NMP) as solvent. Alternatively, a mixture of NMP and aromatic hydrocarbon may be used as the solvent.
It was discovered in the near past that people exposed to NMP may be potentially health-affected. Alternative solvents, such as Tetrahydrofuran (THF), methyl Ethyl Ketone (MEK), gamma-butyrolactone (GBL) or dimethyl sulfoxide (DMSO), are known, but they have the disadvantage of having a boiling point too low to be used as a reaction solvent, a low solubility of the polymer resin or poor storage stability, which may alter the properties of the polymer in the application in which it is to be used.
Although NMP is safe when operated in the correct way and taking sufficient safety and health precautions, various documents relating to alternative solvents have been disclosed, such as those disclosed in US2013/0217812, WO2013/090933, WO2013/107822, US2015/0299393 and WO 2015/144663.
In US2015/0299393 the preparation of polyamideimide resins in alternative lower toxic solvents such as N-formyl morpholine (NFM) and N-acetyl morpholine (NAM) is disclosed. These less toxic solvents (primary solvents) may be used in combination with a co-solvent (or secondary solvent), wherein the amount of co-solvent is lower than the amount of primary solvent. A number of potential co-solvents are mentioned in this document. The polyamideimide resins prepared in this way are said to be useful as coating compositions for wire coatings, but there are no known commercial wire coating systems based on these compositions.
Various solvents that can be used as replacement solvents to replace NMP in wire enamel compositions comprising polyamideimide resins are disclosed in WO 2013/107822. Examples of wire enamel compositions suitable for enamelling copper wire are given in WO 2013/107822. The inventors of the present application repeated the experiments in WO2013/107822 and found that, although some properties of the enameled copper wire using the alternative solvent were comparable to the results obtained using the NMP solvent, the properties of the enameled copper wire using the alternative solvent were generally insufficient to use the composition as a substitute for the NMP-based composition. In particular, the cut-through resistance, ethanol resistance, flexibility and Tan delta do not meet the commercial specifications of NMP-based polyamideimide resin compositions for wire enamel applications.
The present invention relates to a composition which meets all the requirements for a wire enamel composition which is qualified for the true replacement of a solvent comprising NMP.
The composition according to the invention comprises:
55 to 65pbw of N-N-butylpyrrolidone (NBP)
25 to 40pbw of a polyamideimide resin
0 to 20pbw of other Components
Wherein the polyamideimide resin has a Mw between 10000 and 40000g/mol (daltons) and a Mw/Mn ratio between 1.1 and 2.
The invention further relates to the use of such a composition as an insulating material for copper or aluminum conductive materials.
The invention further relates to the preparation of polyamideimide resins in which N-butylpyrrolidone is used as solvent in the presence of a modifier compound to react an anhydride with a diisocyanate at a temperature of 80 to 120 ℃.
The invention further relates to a method for enamelling metal wires with the composition according to the invention.
The polyamideimide resin used in the present invention may be derived from a polycarboxylic acid or anhydride thereof in which two carboxyl groups are located in ortho positions and in which at least one additional functional group must be present, and from a polyamine having at least one primary amino group capable of forming an imide ring, or from a compound having at least 2 isocyanate groups. The polyamideimide can also be obtained by reacting a polyamide, a polyisocyanate containing at least 2 NCO groups and a cyclic dicarboxylic anhydride containing at least one additional group which can be reacted by condensation or addition.
In addition, it is also possible to prepare polyamideimides from diisocyanates or diamines and dicarboxylic acids, provided that one of the components already contains imide groups. For example, it is particularly possible to first react a tricarboxylic anhydride with a di-primary diamine (diprimary diamine) to give the corresponding diiminocarboxylic acid, which is then reacted with a diisocyanate to form the polyamideimide.
For the preparation of polyamideimides, preference is given to using tricarboxylic acids or their anhydrides in which 2 carboxyl groups are located in the ortho position. Preference is given to the corresponding aromatic tricarboxylic anhydrides, for example trimellitic anhydride, naphthalene tricarboxylic anhydride, biphenyl tricarboxylic anhydride, and also other tricarboxylic acids having 2 benzene rings and 2 ortho-carboxyl groups in the molecule, as examples given in DE-A19 56 512. Very particular preference is given to using trimellitic anhydride. As amine component it is possible to use the di-primary diamine already described in connection with the polyamidocarboxylic acid. In addition, it is also possible to use aromatic diamines containing thiadiazole rings, such as 2, 5-bis (4-aminophenyl) -1,3, 4-thiadiazole, 2, 5-bis (3-aminophenyl) -3, 4-thiadiazole, 2- (4-aminophenyl) -5- (3-aminophenyl) -1,3, 4-thiadiazole, and mixtures of the various isomers.
Suitable diisocyanates for the preparation of the polyamideimide are aliphatic diisocyanates such as tetramethylene diisocyanate, hexamethylene diisocyanate, heptamethylene diisocyanate and trimethylhexamethylene diisocyanate; alicyclic diisocyanates such as isophorone diisocyanate, ω '-diisocyanato-1, 4-dimethylcyclohexane, cyclohexane 1, 3-diisocyanate, cyclohexane 1, 4-diisocyanate, 1-methylcyclohexane 2, 4-diisocyanate and dicyclohexylmethane 4,4' -diisocyanate; aromatic diisocyanates such as phenylene diisocyanate, toluene diisocyanate, naphthalene diisocyanate and xylylene diisocyanate, and substituted aromatic systems such as diphenyl ether, diphenyl sulfide, diphenyl sulfone and diphenylmethane diisocyanate; aromatic-aliphatic and aromatic-hydrogenated aromatic diisocyanates, such as 4-isocyanatomethylphenyl isocyanate, tetrahydronaphthalene 1, 5-diisocyanate, and hexahydrobenzidine 4,4' -diisocyanate, are mixed. Preference is given to using 4,4' -diphenylmethane diisocyanate, 2, 4-and 2, 6-toluene diisocyanate and hexamethylene diisocyanate.
It was found that a polyamideimide resin dissolved in NBP which exhibits the necessary beneficial properties for qualifying as wire enamel can only be obtained when the polyamideimide resin is prepared in NBP under well defined reaction conditions. It was found that the reaction temperature should not be too high, preferably in the range of 80 to 130 ℃, more preferably in the range of 80 to 120 ℃. It was found that when the reaction temperature is above 130 ℃, the reaction is too fast and uncontrolled to obtain a polyamideimide resin having a Mw of at least 10000g/mol and a Mw/Mn ratio between 1.1 and 2. When the reaction temperature is lower than 80 ℃, the reaction is so slow (if any) that it cannot be used in practice for producing a polyamideimide resin.
It has further been found to be beneficial to have small amounts of a modifier compound, such as a low molecular weight monoanhydride or monocarboxylic acid, present in the reaction mixture. Examples of suitable low molecular weight monocarboxylic acids include (C1-C10) monocarboxylic acids or C4-C6 branched monocarboxylic acids such as formic acid, acetic acid, propionic acid, etc., examples of suitable anhydrides include phthalic anhydride. The amount of low molecular weight monoanhydride or monocarboxylic acid in the reaction mixture should be 4 to 8 mole% based on the amount of polyamideimide resin formed in the reaction.
The present invention enables the preparation of solutions comprising N-butylpyrrolidone as main solvent and a polyamide imide resin in an amount >21 wt%, said polyamide imide resin having a Mw between 10000 and 40000g/mol (daltons) and a Mw/Mn ratio between 1.1 and 2.
Such a solution may contain other solvents, but the amount of these other solvents is much lower than the amount of N-butylpyrrolidone.
The invention also relates to the manufacture of enamelled wires by using the composition of the invention.
The application and curing of the composition according to the invention does not require any particular or special procedure and conventional application methods can be used. The wire typically has a diameter of 0.005 to 6 mm. Suitable wires include conventional metal wires, preferably copper, aluminum or alloys thereof. The wire shape is not limited, and a circular or rectangular wire may be particularly used. The compositions of the present invention may be applied as a single layer coating, a double layer coating, or a multi-layer coating.
The composition may be applied in conventional layer thicknesses, with dry layer thicknesses being in accordance with standardized values for thin and thick lines. The composition of the invention is applied to a wire and cured in a horizontal or vertical oven. The wire may be coated and cured one to several times in succession. As curing temperature, suitable ranges may vary from 300 to 800 ℃ depending on the conventional parameters for the lacquer and the properties of the wire to be coated. The conditions of the coating, such as number of passes, coating speed, furnace temperature, depend on the nature of the wire to be coated.
In order to enhance the cut-through resistance (cut through resistance) of wires coated with the composition according to the invention, nanoparticles may also be included in the composition according to the invention.
Nanoparticles which can be used in the composition according to the invention are particles whose average radius is in the range from 1 to 300nm, preferably in the range from 2 to 100nm, particularly preferably in the range from 5 to 65 nm. Examples of preferred nanoparticles are nano-oxides, nano-metal oxides, colloidal metal oxides, metal oxides or hydrated oxides of aluminium, tin, boron, germanium, gallium, lead, transition metals and lanthanides and actinides, in particular of the series comprising aluminium, silicon, titanium, zinc, yttrium, vanadium, zirconium and/or nickel, preferably aluminium, silicon, titanium and/or zirconium, which are in the nano-scale in the dispersed phase, can be used alone or in combination. Among the nano metal oxides, nano alumina is most preferable. Examples of nano-alumina are: BYK-LP X20693 of BYK-Chemie GmbH and Nycol AI20OSD of NanoBYK 3610, nycol Nano Technologies lnc, dispel X-25SR and SRL of Sasol Germany GmbH, disperal P2, P3, OS1 and OS2. Among nano-aluminas, ceramic particles of alumina pre-dispersed in a polar solvent, such as BYK-LP X20693 and nanoBYK 3610 of BYK-Chemie GmbH, are preferred.
Nanoparticles may be used with coupling agents. As coupling agent, any well known functional alkoxysilane or aryloxysilane may be used. Of the functional silanes, (isocyanatoalkyl) -trialkoxysilane, (aminoalkyl) -trialkoxysilane, (trialkoxysilyl) -alkyl anhydride, and oligomeric diaminosilane systems are preferred. The alkyl and alkoxy groups of the functional silane have from 1 to 6 carbon atoms, more preferably from 1 to 4 carbon atoms. The above alkyl group and alkoxy group may further have a substituent thereon. Titanates and/or zirconates may also be used as coupling agents. Any of the usual orthotitanates or zirconates may be used, for example tetraisopropyl, tetrabutyl, acetylacetone, acetoacetates, diethanolamine, triethanolamine, cresols titanate or zirconate.
To enhance the dispersion of the nanoparticles in the polymer solution matrix, a coupling agent such as a functional silane, titanate or zirconate may be added directly to the nanoparticle dispersion and mixed therein before loading it into the polymer resin solution or may be added directly to the polymer solution prior to addition of the nanoparticle dispersion. The coupling agent may optionally be mixed into the polymer solution prior to loading the nanoparticle dispersion to better link the inorganic moiety to the organic moiety. The mixture of polymer solution and coupling agent may be stirred at room temperature or at a relatively low temperature for several hours before adding the nano metal oxide solution.
Enamelled wires made according to IEC 60851 test.
Measurement method
Mw is measured in accordance with DIN 55672-2;
mn is measured in accordance with DIN 55672-2;
viscosity was measured according to ASTM D3288;
spindle test (mandril test) was measured according to IEC 60851-part 3.
Ethanol resistance was measured according to IEC 60851-part 4.
The cut-through test was measured according to IEC 60851-part 6.
Tan delta was measured according to IEC 60851-part 5.
The jerk test (jerk test) was measured according to IEC 60851-part 3.
Examples
Example 1 (comparative): experiment 1 from WO2013/107822 was repeated under exactly the same conditions to prepare a solution of polyamideimide in N-butylpyrrolidone (NBP). A polyamideimide solution having an average molecular weight of 7136 g/mol was obtained (sample 1).
Example 2: 18.08 parts by weight (pbw) of trimellitic anhydride, 23.5pbw of 4,4' -diphenylmethane diisocyanate, 0.12pbw of formic acid and 58.29pbw of NBP were loaded in a reaction vessel and heated to 85 ℃. The mixture was kept at 85 ℃ for 2 hours and then slowly heated to 100 ℃. The temperature in the reaction vessel was maintained at this temperature for several hours.
1 hour after reaching 100℃a sample of 10.9pbw was extracted from the reaction vessel and measured for molecular weight 9665 g/mol (sample 2).
The reaction was continued and after an additional 1 hour a further 10.9pbw of sample was taken from the reaction vessel and the molecular weight was measured to be 15593 g/mol (sample 3).
The reaction was continued and after an additional 1 hour a further 10.9pbw of sample was taken from the reaction vessel and the molecular weight was measured to be 16771 g/mol (sample 4).
The reaction was continued and after a total reaction time of 7 hours at 100℃a further sample of 10.9pbw was taken from the reaction vessel and the molecular weight was measured to be 24583 g/mol. This sample was further diluted with benzyl alcohol to reach a viscosity of 13000mPas at 23 ℃ (sample 5).
Example 3: a typical wire enamel test was performed on all samples collected in examples 1 and 2. In this comparison, a commercially available polyamideimide resin solution in NMP (sample 6) was also used. The results of these experiments are shown in table 1.
Table 1: test results
Sample of
R: requirements for commercial use
* ) Comparative example
Claims (8)
1. A composition comprising
55 to 65pbw of N-N-butylpyrrolidone,
25 to 40pbw of a polyamideimide resin,
0 to 20pbw of other components,
characterized in that the polyamideimide resin has a Mw between 10000 and 40000g/mol (daltons) and a Mw/Mn ratio between 1.1 and 2.
2. The composition of claim 1, further comprising nanoparticles having an average diameter in the range of 1 to 300 nm.
3. The composition of claim 1, obtainable by reacting a mixture comprising a tricarboxylic acid having 2 ortho-carboxyl groups or an anhydride thereof, a diisocyanate, a regulator compound and N-butylpyrrolidone at a temperature of 80-120 ℃.
4. A process for the preparation of a polyamideimide resin, wherein a mixture comprising a tricarboxylic acid having 2 ortho-carboxyl groups or an anhydride thereof, a diisocyanate, a regulator compound and N-butylpyrrolidone is reacted at a temperature of 80-120 ℃ until a polyamideimide resin is obtained having a Mw in the range of 10000 to 40000g/mol (daltons) and a Mw/Mn ratio of between 1.1 and 2.
5. The method according to claim 4, wherein the modifier is a low molecular weight monocarboxylic acid.
6. The process according to claim 5, wherein the low molecular weight monocarboxylic acid is selected from the group consisting of formic acid, acetic acid and propionic acid.
7. The method according to any one of claims 4-6, wherein the mixture further comprises nanoparticles having an average diameter in the range of 1 to 300 nm.
8. A method of coating a metal wire, wherein the wire is coated with the composition of claims 1-3.
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2021
- 2021-09-20 CN CN202180064490.XA patent/CN116194513A/en active Pending
- 2021-09-20 WO PCT/EP2021/075752 patent/WO2022063715A1/en active Application Filing
- 2021-09-20 JP JP2023518244A patent/JP2023542189A/en active Pending
- 2021-09-20 US US18/026,152 patent/US20230287180A1/en active Pending
- 2021-09-20 KR KR1020237009290A patent/KR20230052939A/en unknown
- 2021-09-20 EP EP21778122.8A patent/EP4217413A1/en active Pending
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US20230287180A1 (en) | 2023-09-14 |
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